Di-acylacetyl-arylenediamine and process of making same



Patented June 28, 1927.

UNITED STATES PATENT" OFFIXCE.

ARTHUR zr'rscnnn AND ROBERT scnmrr'r, or omnNmcn-on-rnn-unm, GERMANY,

ASSIGNORS TO I. G. sansnmnnusrnxn nx'rmnensnnnsonnrr, or rnnnxron'r- ON-THE-MAIN GERMANY.

DI-ACYLAOETYL-ARYLENEDIAMINE AND PRQCEBS OI MAKJ ING SAME;

No Drawing.

Our invention relates to new di-ac lacetyldiamino compounds of the general ormula:

Y co-cnr-co-Nm-ar lene-Nn'oo-cHro -Y,

wherein Y means any radicle of the-hydrocarbon series containing atleast one and not more than six carbon atoms, this term including aliphatic as well as aromatic radicles.

The process of making the new,compounds consists in heating arylenediamines, such as- 4 Example.

Into a mixture,'heated to about 180, of

Application filed May is, i923. Serial Io. 039,215.,

205 parts of acetoaceti'c acid ester and 200 parts of nitrobenzene 36 dparts ofpara-phenylenediamine are poure slowly whilestirring. The mixture is held at this temperature for sometime and then allowed to cool.

The yellow crystalline precipitate, formed after cooling down, is filtered, washed with A ether and dried. For purifying the resultng di-acetoacetyl 1.4-phenylenediamine is crystallized from a very dilute aqueous solution and obtained in form of'fine, colorless needles, melting at-167 with decomposition.

It is soluble in water and alcohol.

Instead of acetoacetic acid ester its'homologues and analogues, suchas benzoylacetic acid ester can be used, with other dismines the process can be conducted'in asimilar manner. a

' In the following table the-properties of some of the compounds obtainable accord: ing to the present process'are described:

Solubility.

cm-co-om-oomn-m hmylm-nmoo-om ooom. The formula of di-aoetoacetyl-l.4.-naphthylenediamine is NH-CO-CHs-CO-CHscm-oo-cal-co-rin I t0. Di-acylaeetyl-compound. A p 0175mm l a-3%. not

Di acetoaoetyl-lA-phenyl- Fine,colorlessneedlssnn.-. Water 167 under deeomposi- Soluble inwetel 'end alcohol.

enediamine. flan.

Di -acetoseetyl -l.4'- naph- Colorless teebly lustrous Aestunitrll- 1W under decomposl- Soluble ln seetonltril, less tion soluble in alcohol glacial thylenedlemine. asls'iaped clusters of no m ad You. V

a L i 1 Glacial eeetio manna-2w under deeom- Solublein ads! and ih lge d dIlLa mph al e f lustrous position. less solubsinsleohol.

5..- Alcohol axe-204' under deeom- Solublelnaleoholand glacial Dzhyrilggtoaeetyla'ze naph Clusters ollustrous nesdl Mum flu M I The formula of di-acetoacetyl-Lfi-nsph thylenediamine is D Y Y Nn-oo-onvoo-on,

thylenediamine is I mr-omom'omom eneoo-om-oo-mz- Now what we claim and desire to secure by Letters Patent is the following:

1. A process of making di-acylacetyl-arylenediamines consisting in heating acylacetic 5 acidesters with arylenediamines.

2. As new articles the di-acylacet l-diamino compounds of the general formu a:

cm-co-cm-co-NH- na im hne--NB-co-om-co-cm.'

4. As a new article 'di-acetoacety1-2.6--

naphthylenediamine oi the formula:

g Nn-oo-cm-co-cm cmco-cm-oo-Nn I 5. A process of making di-acxlacetyl-arylenediamines, which consists in eating acylacetic acid esters with arylenediamines in the presence of a diluent. 

